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E-Configuration Improves Antioxidant and Cytoprotective Capacities of Resveratrols.

ABSTRACT: The antioxidant and cytoprotective capacities of E-resveratrol and Z-resveratrol were compared using chemical and cellular assays. Chemical assays revealed that the two isomers were dose-dependently active in •O?^--scavenging, ferric reducing antioxidant power (FRAP), Cu²⁺-reducing antioxidant capacity (CUPRAC), 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide radical (PTIO•)-scavenging (pH 7.4 and pH 4.5), and 1,1-diphenyl-2-picryl-hydrazyl (DPPH•)-scavenging assays. The cellular assay indicated that the two isomers could also increase cell viabilities. However, quantitative analyses suggested that E-resveratrol exhibited stronger effects than Z-resveratrol in all chemical and cellular assays. Finally, the conformations of E-resveratrol and Z-resveratrol were analyzed. It can be concluded that both E-resveratrol and Z-resveratrol can promote redox-related pathways to exhibit antioxidant action and consequently protect bone marrow-derived mesenchymal stem cells (bmMSCs) from oxidative damage. These pathways include electron transfer (ET) and H?-transfer, and likely include hydrogen atom transfer (HAT). The E-configuration, however, improves antioxidant and cytoprotective capacities of resveratrols. The detrimental effect of the Z-configuration may be attributed to the non-planar preferential conformation, where two dihedral angles block the extension of the conjugative system.

SUBMITTER: Lin J

PROVIDER: S-EPMC6100583 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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E-Configuration Improves Antioxidant and Cytoprotective Capacities of Resveratrols.

Lin Jian J Li Xican X Chen Ban B Wei Gang G Chen Dongfeng D

Molecules (Basel, Switzerland) 20180720 7

The antioxidant and cytoprotective capacities of E-resveratrol and Z-resveratrol were compared using chemical and cellular assays. Chemical assays revealed that the two isomers were dose-dependently active in •O₂--scavenging, ferric reducing antioxidant power (FRAP), Cu2+-reducing antioxidant capacity (CUPRAC), 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide radical (PTIO•)-scavenging (pH 7.4 and pH 4.5), and 1,1-diphenyl-2-picryl-hydrazyl (DPPH•)-scave ...[more]

PMID: 30036971

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Project description:Tibetan tea (Kangzhuan) is an essential beverage of the Tibetan people. In this study, a lyophilized aqueous extract of Tibetan tea (LATT) was prepared and analyzed by HPLC. The results suggested that there were at least five phenolic components, including gallic acid, and four catechins (i.e., (+)-catechin, (-)-catechin gallate (CG), (-)-epicatechin gallate (ECG), and (-)-epigallocatechin gallate). Gallic acid, the four catechins, and LATT were then comparatively investigated by four antioxidant assays: ferric reducing antioxidant power, 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide radical (PTIO•) scavenging, 1,1-diphenyl-2-picryl-hydrazl radical scavenging, and 2,2'-azino-bis(3-ethylbenzo-thiazoline-6-sulfonic acid) radical scavenging assays. In these assays, LATT, along with the five phenolic components, increased their antioxidant effects in a concentration-dependent manner; however, the half maximal scavenging concentrations of ECG were always lower than those of CG. Gallic acid and the four catechins were also suggested to chelate Fe2+ based on UV-visible spectral analysis. Ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q-TOF-MS/MS) analysis suggested that, when mixed with PTIO•, the five phenolic components could yield two types of radical adduct formation (RAF) products (i.e., tea phenolic dimers and tea phenolic-PTIO• adducts). In a flow cytometry assay, (+)-catechin and LATT was observed to have a cytoprotective effect towards oxidative-stressed bone marrow-derived mesenchymal stem cells. Based on this evidence, we concluded that LATT possesses antioxidative or cytoprotective properties. These effects may mainly be attributed to the presence of phenolic components, including gallic acid and the four catechins. These phenolic components may undergo electron transfer, H⁺-transfer, and Fe2+-chelating pathways to exhibit antioxidative or cytoprotective effects. In these effects, two diastereoisomeric CG and ECG showed differences to which a steric effect from the 2-carbon may contribute. Phenolic component decay may cause RAF in the antioxidant process.

Project description:BackgroundHimalayan plants are widely used in traditional system of medicine both as prophylactics and therapeutics for high altitude maladies. Our aim was to evaluate the antioxidant capacities and bioactive compounds of methanol and n-hexane extracts of the phytococktail comprising of sea buckthorn (Hippophae rhamnoides), apricot (Prunus armeniaca) and roseroot (Rhodiola imbricata) from trans-Himalaya.MethodsThe 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS) and nitric oxide (NO) radical scavenging capacities and lipid peroxidation inhibition (LPI) property of the extracts were determined. Total antioxidant power was determined by ferric reducing/antioxidant power (FRAP) assay. Total polyphenol, flavonoid, flavonol, proanthocyanidin and carotenoid were also estimated for both extracts. We have identified and quantified the phyto-chemotypes present in the methanol and n-hexane extracts by hyphenated gas chromatography/mass spectrometry (GC/MS) technique.ResultsAntioxidant capacity assays using DPPH, ABTS, NO, LPI and FRAP exhibited analogous results where the phytococktail showed high antioxidant action. The phytococktail was also found to possess high quantity of total polyphenol, flavonoid, flavonol and carotenoid. A significant and linear correlation was found between the antioxidant capacities and bioactive principles. A total of 32 phyto-chemotypes were identified from these extracts by GC/MS chemometric fingerprinting. Major phyto-chemotypes identified by GC/MS were glycosides, phenylpropanoids and derivatives, terpenoids, alkaloids, phytosterols, fatty acids and esters, alkaloids and derivatives, organic acid esters and aromatic ethers with positive biological and pharmacological actions.ConclusionThe phytococktail extracts were found to contain considerable amount of diverse bioactive compounds with high antioxidant capacities. The presence of hydrophilic and lipophilic antioxidants in the phytococktail could have contributed to the higher antioxidant values. Hence, the phytococktail could be used as natural source of antioxidants to ameliorate disorders associated with oxidative stress.

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E-Configuration Improves Antioxidant and Cytoprotective Capacities of Resveratrols.

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<i>E</i>-Configuration Improves Antioxidant and Cytoprotective Capacities of Resveratrols.

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